Singapore takes off its corporate mask after sunset – Clarke Quay gets busy, the river reflects a thousand lights, and the people stop pretending. Only a few directors really understood that side of the city, and Eric Khoo was first among them with 1995’s Mee Pok Man.

A mute noodle vendor lives in a cramped HDB flat, in love with Bunny, a prostitute working near his stall. Khoo shot in real red-light districts with harsh fluorescents and tight frames, showing Singapore’s underbelly as it is. But when the vendor finds Bunny injured and brings her home, his warped sense of care turns the film deeply uncomfortable.

It hit Venice, Berlin, Rotterdam, and 60 other festivals, earning Khoo the Special Jury Prize at Fukuoka and FIPRESCI recognition.

Two years later, he made 12 Storeys, which got invited to Cannes – the first time for any Singapore production. The whole thing takes place in one HDB block over a single day: three families, three messed-up situations. Khoo won the FIPRESCI Award at SGIFF and Best Picture in Hawaii.

Sandi Tan, on the other hand, tried to make Singapore’s first road movie in 1992 – she was only 19, wrote a scenario about a young assassin, and got her friends to produce it. Their American film teacher, Georges Cardona, agreed to direct and handle cinematography. But after shooting for two and a half months on 16mm film, Cardona vanished with all 70 reels. Gone. Tan then moved to the US, became a novelist, and tried to forget about it.

In 2011, the footage somehow showed up at her door, so she turned the whole mess into a documentary called Shirkers, investigating what happened and who Cardona really was. Tan took the Directing Award at Sundance 2018.

Even though she was piecing together the ‘’traditional’’ Singapore of the 90s, the city itself had already started drifting into something closer to science fiction. Marina Bay Sands is now in every fresh shot, those three towers as a postcard of the city and the country. The casino inside might be the perfect example of the scale itself – 700 tables, over a thousand slots, open 24 hours.

People come in after dinners and late meetings, sit down, play for a few hours, and move on. Poker tables run through the night, but the experience still has its downsides: dress codes at the door, a $150 local entry levy, and cashouts only in banking hours that do not always match the pace of the city outside.

That said, more players end up spending more time online, where poker rooms spell things out clearly, explaining all the details about easy crypto payments, the growing player base, weekly leaderboards, and generous prize pools before a session even starts. It’s a contrast that says as much about how the city moves nowadays as the stories filmmakers keep returning to.

Yeo Siew Hua’s A Land Imagined came out in 2018 and took home the Golden Leopard at Locarno – the first Singapore film to win that. A detective searches for Wang, a Chinese migrant worker who vanished from a land reclamation site, and the film cuts between the investigation and Wang’s final days spent gaming at a cybercafé with insomnia that didn’t let him rest.

Interestingly, Singapore has grown its landmass by 22% since 1965 by importing sand from Malaysia, Indonesia, and Cambodia. Yeo uses that fact as a foundation for the film’s central question: what does it mean to stand on ground that belonged somewhere else, worked by people who’ll never belong here? The film also won Best Asian Feature at SGIFF and became Singapore’s Oscar submission that year.

Eric Khoo returned in 2015 with In the Room: six stories through six decades, all set in the same hotel room, but each showing a different layer of the city’s hidden life. A 1940s goodbye between two men as the Japanese arrive, a 1960s brothel madam played by Josie Ho instructing her girls on handling clients, a 1980s affair between a Japanese housewife and her Singaporean lover, a 1990s Korean couple arguing whether sex matters more than emotional connection – that segment features Choi Woo-shik years before Parasite made him famous.

Khoo dedicated the film to Damien Sin, who wrote Mee Pok Man and died of an overdose, and when the censorship board blocked it over two scenes, Khoo refused to cut anything. A slightly adjusted version finally secured an R21 rating in 2016, but the fight itself became part of the film’s legacy.

What connects these films goes beyond geography, rooted instead in their refusal to accept Singapore’s official story. They show migrant workers in cramped dorms, families disintegrating in public housing, red-light districts operating in plain sight, hotel rooms accumulating decades of secrets… Khoo, Tan, and Yeo stayed with the city once its guard fell.

None of them made it easy on themselves either – Khoo spent his entire career fighting censors, Tan waited 26 years to finish her project, and Yeo built a film around people mainstream Singapore would rather not see. They shot in places that don’t appear on postcards and told stories without clean resolutions or comfortable morals, and that stubbornness produced the most accurate record of what this city actually looks like when the performance ends.

Most of these won’t play at Orchard Road multiplexes. You have Shirkers and A Land Imagined on Netflix, while the search for older Khoo films takes some time, but it’s worth finding if you want the Singapore that exists between midnight and sunrise when the lights stay on.